Two couples and their single friend, all at different stages in their relationships, deal with the complications of dating, commitment, and marriage...Jeff unsuccessfully tries to keep Russell from sleeping with their new surrogate, while Adam tries to work on improving his rear end...Audrey contemplates her career as she plays on Jeff's softball team, Timmy becomes frustrated after his girlfriend cuts him off, and Adam and Jennifer try to come up with an interesting fictional story about how they met...Jeff struggles to figure out how to ask his co-workers to donate money for Audrey's 10K charity run after telling them that he doesn't want to participate in their fundraisers anymore. Meanwhile, Russell gets a taste of his own medicine from a recent date...Russell mistakenly books a spot on a cruise filled with "Red Hat" women, Jeff and Audrey turn to the videotape to settle their latest fight, and Adam and Jennifer accidentally ruin Jeff and Audrey's paint job and couch...
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